1-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,2-dihydropyridin-2-one

• ChemBase ID: 165475
• Molecular Formular: C10H13NO6
• Molecular Mass: 243.21332
• Monoisotopic Mass: 243.07428714
• SMILES: c1cn(c(=O)cc1O)[C@H]1C([C@H]([C@H](O1)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1O)O)n1ccc(cc1=O)O
• InChI: InChI=1S/C10H13NO6/c12-4-6-8(15)9(16)10(17-6)11-2-1-5(13)3-7(11)14/h1-3,6,8-10,12-13,15-16H,4H2/t6-,8+,9?,10-/m1/s1
• InChIKey: CBOKZNLSFMZJJA-UKUJCULDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,2-dihydropyridin-2-one
• IUPAC Traditional name: 1-[(2R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxypyridin-2-one
• Synonyms: 4-Hydroxy-1-β-D-ribofuranosyl-2(1H)-pyridinone; 1-β-D-Ribofuranosyl-4-hydroxy-2-pyridone; 3-Deazauridine; 3-Deazuridine; 4-Hydroxy-1-(β-D-ribofuranosyl)-2-pyridone; NSC 126849; 3-Deazauridine

Database IDs

• CAS Number: 23205-42-7
• PubChem SID: 162259608
• PubChem CID: 71315225

CALCULATED PROPERTIES

• Acid pKa: 8.844985
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.942299
• LogD (pH = 7.4): -1.9574134
• Log P: -1.9421028
• Molar Refractivity: 56.5339 cm^3
• Polarizability: 21.80971 Å^3
• Polar Surface Area: 110.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D203240

Antimetabolite antiviral dosing regimen for hepatitis C virus or flaviviridae therapy.

REFERENCES

• Teh, A.-H., et al.: Biochemistry, 45, 7825 (2006)